Gigolo to the Stars

===DISCLAIMER===

This is a work of erotic fiction.

The person(s) portrayed in this work are over the age of 18.

This material should not be viewed by any parties under 18 years of age.

Copyright: YoungDubz 2023

= = =

Chapter 4

A woman barged her way into Jake's hotel room and sat down on the bed.

"It's Jake, right? I have a proposal for you!" Said Aubrey Plaza,

Jake, still half asleep but intrigued, looked at the stunning woman on his bed at such an early hour. She was dressed as if attending a business meeting. She wore a black pencil skirt which came down to mid thigh on her long legs, the top of her black stockings visible as she crossed her legs on the bed. On her upper body, she wore a white shirt under a black blazer, the top 3 buttons undone to slightly show her cleavage. Her long dark hair was done up in a professional looking bun and her captivating eyes were framed by a pair of glasses. She'd done her makeup also, subtle dark eyeliner and her lips a shade of bright red. She carried a laptop bag over her shoulder, which she put down on the bed next to her.

"What kind of proposal?" Jake asked the sultry brunette, sitting in his bed leaning back on her arms.

"Let me help you with your whole bimbo fucking business!" replied Aubrey.

"Help how?" Asked Jake, curiously.

"I heard about you from Mary, she messaged me after you left. Evidently, you made quite the good impression with her and her little plaything last night. She told me what you've been doing and I instantly knew what you needed. You need efficiency, you need management. Essentially, your dick needs an agent and I'm here to put myself forward for the role." Said the raven haired beauty.

"An agent? And what would that entail, exactly?" Asked Jake.

"Give me your phone, the one all these tramps have been messaging and I'll show you." Said Aubrey.

Jake went over to the bedside table, and picked up his work phone.

Jake unlocked and handed the phone over to Aubrey.

She took the phone, and took a MacBook from her shoulder bag. She scrolled through the phone, typing information into the laptop as she did so and replying to messages.

Jake watched Aubrey in action, the concentration on her face making her somehow look more beautiful.

Aubrey soon locked the phone again, and looked to Jake.

"And voila!" She said, spinning the laptop toward Jake.

He stepped closer and studied the day calendar Aubrey had set up. She has split his day up into 5 or 6 blocks of about three hours each, the last ending at 11pm that evening.

"Follow this, that should be two and a half, three thousand you'll have made today." Said Aubrey.

Jake studied the schedule Aubrey had created.

He looked at the brunette. "So, if I go along with this, what exactly is in it for you? I'm assuming you're after a cut?"

"Every good agent has their rate, honey. Ten percent for the day is mine." Replied Aubrey. "I know for privacy's sake, you're paid in cash, I'm happy to take the same."

"I'm not agreeing, but I'm willing to call today a trial run and we'll see how it goes." Said Jake.

"If that's what it takes." Said Aubrey.

Jake looked again at the schedule. In his not fully awakened state, he hadn't looked at the blocked out sections fully. When he did, he turned to Aubrey with a question

"So, I can't help noticing there's a session here that looks to already be in progress." Jake said, studying the laptop. "Is that for you, I take it?"

Aubrey rose from the bed and started to undo her blazer. "Well, I've not come all this way just to offer to be a glorified secretary. I figured I would at least sample what you got to offer. The way Mary described how that cock felt, I have to try you out for myself!" she said, as she continued removing her clothes. Her shirt and skirt had both been discarded, leaving the dark haired Parks and Recreation star in a black lace two piece lingerie set and black stockings. She undid her hair and let the dark tresses fall to her shoulders.

Jake stood up and Aubrey kissed him on the mouth, her tongue probing between his lips until they parted. The two French kissed in the middle of the room, until Jake moved and pushed Aubrey against the nearby wall. His hands on her hips, he held her there as the kiss was broken. Aubrey raised a hand to remove her glasses, but Jake stopped her.

"Leave them on!" He growled at her.

Aubrey complied, leaving the glasses on her face. She moaned as Jake started to kiss her neck and collarbone, long time erogenous zones for her. The way Jake nibbled, kissed and sucked on her skin driving Aubrey crazy.

"Mmmm, bite me! Leave a fucking mark on me, you know you want to!" Groaned Aubrey, followed by a deep moan as Jake did as requested. He bit down on her shoulder, hard enough to leave a mark but not break the skin. Aubrey shuddered with desire, her hand reaching down to rub Jake's hardening penis through his shorts.

Jake followed this up by kissing down to her petite breasts. He kissed Aubrey's chest between the two mounds of flesh, and reached behind her to undo her bra.

He unhooked the item and pulled it away from Aubrey's body with his teeth and dropped it to the floor, then latched himself onto one breast while his hand played with the other. He sucked on Aubrey's nipple, feeling it get harder in his mouth while his hand kneaded the soft flesh of her other breasts, pinching that nipple between his fingers.

Knowing how she liked being bitten on her shoulder, Jake did the same to each nipple, causing the dark haired beauty to squeal and moan.

"Oooh, fuck yes. That's what I like! Keep biting me, bite me while I stroke this hard fucking cock!" purred Aubrey, as she reached her hand into Jake's shorts and gripped his fully hard penis. She started to rub her hand up and down his shaft, quickening her pace as Jake gave her nipples another bite each.

The pair kept this up for a few minutes, before Jake started kissing a path down from Aubrey's breasts, down her toned stomach. This caused Aubrey to stop jerking his cock, as it moved out of her reach. Jake swirled his tongue in Aubrey's belly button, causing the Legion star to giggle, before he continued and reached the top of her panties.

He used both his hands to take hold of and pull Aubrey's panties down her long, smooth stockinged legs, rubbing a leg with one hand each as he moved them both back up to Aubrey's hips.

Her pussy now exposed, Jake studied it briefly, the hairless mound glistening with the evidence of her arousal. He blew onto Aubrey's pussy, causing the actress to moan loudly, before he dove in and started to fuck her tight hole with his tongue.

"Fuuuuuck. Fuuck, you're good at that!" moaned Aubrey. "Lick my cunt, man whore! Tongue my fucking pussy, make me cum on that tongue!"

Jake listened to Aubrey's aroused demands, and considered keeping her waiting as revenge for waking him up, but as he thrust his tongue in and out of her tight hole, he found her flavour too good to pass up.

Jake kept licking Aubrey's pussy, before getting a wicked idea. He pulled away from her pussy and with both hands on her hips, he turned Aubrey around against the wall, and pulled her ass cheeks apart, exposing her little ass hole.

He resumed licking at the wet pink hole, and when he thought the time was right, he licked from Aubrey's clit, and up to her little anal ring.

"Mmm, god yes, rim my fucking asshole. Stick your tongue in my little asshole. Fucking spank my ass while you do it, make my fucking asscheeks pink!" Ordered Aubrey.

Not one to resist an order, Jake withdrew both hands from Aubrey's cheeks, pulled back with both of them and as hard as he could he struck both cheeks, a red hand mark remaining as he pulled his hands away again and repeated the move.

Jake did this a third time, then ran his hands around Aubrey's waist and onto her pussy. His fingers ran along the slick wetness of her pussy, then Jake curled two of them inside.

"Mmm, fuck yes, finger my tight, wet cunt while you tongue fuck my ass. Oh god, make me fucking cum on those fingers!" Moaned Aubrey, moving her hips in an attempt to get more of Jake's tongue and fingers inside her holes.

Jake obliged, and quickened the speed of his fingers pumping in and out of Aubrey Plaza's wet pussy, and rapidly flicking his tongue against her tight, puckered asshole.

This had the desired effect, and Aubrey's orgasm soon came. Her upper body still pressed against the wall, Aubrey shook and screamed as she came.

"FUUUUUCK YEESS! FUCKING CUMMING FOR YOU, ALL OVER THOSE FUCKING MAGIC FINGERS! GODDDDDD DAMMIT, YES!" Screamed Aubrey, almost collapsing as the pleasure ran through her entire body, only remaining upright as Jake held her in position.

Jake rose from his position on the floor, pushing his shorts down to expose his cock whilst holding on to Aubrey's waist. He took hold of his cock and rubbed it against her wet entrance.

"Wait," Mumbled Aubrey, who turned around, put her arms around Jake's neck, and used what energy she currently had to jump up, wrapping her smooth stocking clad legs around his waist. "Fuck me against the wall like this!"

Jake put one arm under Aubrey's ass to support her, while he used his other hand to position his cock at her wet hole. He pushed forward, his cock entering Aubrey Plaza's pussy for the first time. Aubrey's pussy was wet enough that Jake was able to push his entire length into her on the first stroke, the feeling causing Aubrey to cum again immediately.

"OHHH GOOOD! YOUR COCK IS SO FUCKING DEEP! POUND THAT PUSSY WITH YOUR HARD FUCKING COCK!" Shouted Aubrey, before silencing herself by biting Jake on his shoulder.

Jake pumped himself in and out of Aubrey against the wall as she came again, the way her wet pussy hugged his cock tightly causing him to feel ecstasy of his own.

"You're so fucking tight!" Groaned Jake, which roused Aubrey from her post-orgasm stupor. She lifted her head and looked at Jake, eyes filled with desire behind the glasses on her face. Studying his face, she could see he was straining to keep them both upright.

"Take us to the bed." Said Aubrey.

Jake did as he was told, carrying Aubrey over to the bed, his cock still within her wet pussy.

"Lie down, let me ride this beautiful cock!" Barked Aubrey.

Jake again followed Aubrey's command, first sitting in the bed then moving them both over so he was lying down.

Aubrey pulled herself off Jake's cock, and sat down between his feet. She moved her stocking covered feet up to Jake's cock, and placed one either side of his shaft. She put her feet together around the hard cock, and started to give Jake a footjob, her feet moving up and down his shaft.

Jake moaned as the soft fabric of the stockings touched his sensitive member. He remembered how good the footjob Karen had given him felt, and this was infinitely better.

"Yes, jerk my fucking cock with those pretty feet. This feels amazing, you sexy fucking bitch."

Aubrey started to pump her feet up and down on Jake's cock faster and faster, her toes rubbing the bulbous head as they passed it.

The faster Aubrey went, the closer Jake felt his orgasm getting.

"Mmm, keep doing that, I'm gonna ruin those fucking stockings!" Jake groaned, causing Aubrey to pause.

"Nuh uh, Jakey, you're not gonna cum just yet! There's more I wanna do with this cock first!" said Aubrey, shifting herself and crawling up Jake's body, until the swollen tip of his cock was rubbing at her wet pink hole. Aubrey reached down, held Jake's cock steady at the entrance to her pussy, and dropped herself down onto it.

In this new position, Aubrey started grinding her hips back and forth on Jake's cock.

"God, that feels amazing. Ride my cock, Aubrey. You're fucking gorgeous!" Moaned Jake.

Aubrey smirked at Jake, and started grinding faster and faster.

She took his hands that he had placed on her hips, and bought them up to her neck.

"Choke me! I don't want any of that "You're gorgeous" bullshit, fucking do it!" Said Aubrey, her voice dripping with passion.

Jake hesitated briefly, but then put his hands around Aubrey's throat and started to squeeze.

This action caused Aubrey to go even faster riding Jake's cock. Instead of grinding back and forth, she was squatting over him and bouncing herself up and down Jake's shaft. Her hands were running over Jake's chest, her fingernails clawing at his skin as she did so.

The feeling of Jake's cock going deep into her pussy, coupled with the euphoric feeling she felt from her breathing being restricted was bringing a third orgasm closer for Aubrey.

"MMM, YES! GONNA CUM AGAIN!" Rasped Aubrey, her throat still being squeezed by Jake.

Aubrey bounced up and down, faster and faster. In her frantic movements, Jake's cock was fully removed from her pussy.

Taking one hand off Aubrey's throat, Jake went to position his cock back at the entrance to the former April Ludgate's pussy.

"Noo, stick it in my ass!" Growled Aubrey, who rubbed her fingers against her wet pussy then moved them behind herself and rubbed her juices against her asshole.

Aubrey still on top of him, Jake positioned the head of his cock, shining with Aubrey's juices, at her tight sphincter and pushed his cock forward, opening her little asshole for him.

As his cock pushed into Aubrey's asshole, inch by inch being swallowed by the tight hole, Aubrey rubbed her pussy, her swollen clit protruding from its hood at the top of her wet lips.

She pushed down on the little pink nub as her asshole was stretched by Jake's long cock, giving herself a third orgasm, her cum shooting out over Jake's chest.

Though Aubrey's asshole got tighter as she came, Jake persevered with inserting his cock into it, the restrictions feeling wonderful for him.

Jake soon bottomed out, Aubrey's firm asscheeks resting against his thighs, the entire length of his cock deep within the beautiful actress's ass.

Her orgasm subsiding, Aubrey started to lift herself up and down on Jake's cock.

"Oh god, yes, I love that big cock in my tight little ass. Fucking fill my ass with that big dick!" Groaned Aubrey, who was slapping her own breasts as she rode Jake's cock.

"Feel so good in that ass!" Moaned Jake. He'd removed his hands from Aubrey's neck and was running them along the slim stocking clad legs of the dark haired beauty.

The two settled into a steady rhythm, the only sounds in the room being their moans of passion and the sound of Aubrey's asscheeks slapping on Jake's thighs.

Aubrey soon spoke up. She leant down, her face close to Jake's ear. She whispered to him as she bounced on his cock.

"How do you like that ass? Nice and fucking tight for you? Much better to fuck than that loose fucking hole of that Kendrick slut, isn't it? What about Hermione's little fucking shitter, is mine better than hers? Or that Scottish bitch, her butt isn't as good as mine, is it? That's right, I've done my research on you, Jake, good and proper! Mary told me about you and I rang around. I've heard all about what you've been doing. What did it feel like to have your cock deep in Emma's throat? When you finger fucked Karen in that bathroom, did you wish it was your cock? I bet you did, this big fucking dick just needs to be in any famous sluts holes, doesn't it? That's where it belongs! That's what I can help you with! I know a hell of a lot more desperate Hollywood skanks who'd pay for a couple hours with this cock, pounding their tight fucking holes. I even know some who've never had a proper cock inside them, would you like that? Being the first to stick their dick in some cherry cunt? Stretching those fresh pussies out, giving those tight cunts their first proper fucking!" Purred Aubrey.

"God, yes, that sounds incredible!" Moaned Jake, feeling own orgasm approaching as Aubrey spoke. His thrusting in Aubrey's ass increased in pace, driving the beauty on top of him crazy. Thinking of what Aubrey requested from him earlier, he put his mouth to her neck,and bit down.

"Gooodd, yes. Bite me, fucking mark me! Mmm, bite my neck while you pound my ass. Ruin my asshole! Make me feel it! Punish me for bursting into your room at the crack of dawn! Slap me, I know you want to! Slap my face, or my tits, even my cunt! Yes, slap my cunt! It's so fucking sensitive!" Screamed Aubrey.

Jake, lost in his own ecstasy, did as requested. He slapped Aubrey across the face with as much strength as he could spare, then each of his breasts before slapping downwards on Aubrey's pussy, the main point of impact being her throbbing clitoris.

This sparked another orgasm in Aubrey, her most intense yet.

"GOD FUCKING YES DAMMIT! GOOOOD, FUCKING CUMMING! YESSSS, AAAARGH!" She screamed, her moans quickly devolving into guttural noises. The intensity of her orgasm caused her whole body to shake and gyrate wildly. She jumped off Jake's cock, his whole length withdrawing for her in one go.

Though her body was pulsing with the aftershocks of her orgasm, Aubrey maintained some sense of urgency with herself, and moved so she could take Jake's cock in her mouth.

Jake watched as Aubrey opened her mouth wide, and in one movement took his cock all the way.

Learning from earlier what Aubrey liked, Jake used one hand to keep Aubrey's head down on his cock, and his other hand pinched her nose, closing her nostrils.

Jake grabbed a handful of Aubrey's hair, and holding her on his cock, he moved them both so he was now standing and Aubrey was on her knees.

Jake kept his cock in Aubrey's throat whilst pinching her nose shut until she tapped on his thighs, then he pulled his cock from her mouth.

Aubrey deeply gasped for air, a mouthful of saliva running from her mouth and onto her breasts. She looked up at Jake with lust.

"Again. Stick this big cock down my throat again!" Demanded Aubrey, grabbing hold of Jake's cock and rubbing her hand up and down the shaft.

Aubrey opened her mouth again, and Jake pushed his cock inside, hearing Aubrey gag as he hit the back of her throat. Jake again shut Aubrey's only airway, pinching her nostrils closed.

Jake looked down as the stunning dark haired actress, locking eyes with her as he began to thrust his cock in and out of her throat, Aubrey not allowing her lips to leave his cock even for a second so no air could get in.

As Jake started to fuck the face of the Parks and Rec actress, Aubrey moved one hand down to her pussy. She rubbed herself as she choked on cock, one of her favourite things to do with a partner

As her throat was penetrated over and over by the thick cock, Aubrey started to finger her pussy.

She inserted two fingers between her wet lips and curled them upwards, rubbing her G-Spot while Jake's cock went back and forth in her mouth.

Tears filled her eyes as her throat was fucked.

Jake withdrew from her mouth again.

Another mouthful of saliva dripped onto Aubrey's modestly sized chest as she swallowed oxygen to get her breath back.

She took Jake's cock in her hand and started to jerk him off.

"You gonna cum, Jake? You wanna cum on this pretty face, huh? What about my tits? Look at them, all shiny with my spit. How about you shoot your load on these perfect little tits and I leave it to dry and go about my day, my chest caked in your dry cum? I have some meetings to go to, it would be so hot to sit with all these executives, my tits covered in hot semen and they wouldn't know it." Said Aubrey, looking up at Jake.

"Mmm, fuck, yeh. Gonna cum, all over that beautiful fucking face!" Jake grunted.

Jake fought to hold his orgasm back, but his floodgates soon opened. He took his cock from Aubrey, jerking it as he held her in place by the hair and quite quickly, streams of his cum shot out and landed on Aubrey's face, covering the glasses on her face. Some hit her on the nose, and the remainder he shot onto her forehead. Jake shot more than he expected, and once he finished, Aubrey's face was covered. Aubrey continued fingering her pussy as Jake cum, her own orgasm coming as the last few shots of his load hit her face.